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Trump: The Art of the Deal by Donald Trump and Tony Schwartz

This book is the first autobiography written by Donald J. Trump, ghostwritten by Tony Schwartz, published in 1987. It provides some insight into Trump's real estate deals and his forays to the world of gambling and sports.

This review is not about that book. It is a review of a novel, written by Tony Schwartz, about a young entrepreneur named Donald J. Trump, who tries to get ahead in the world of wealth and status, mapping out the boundaries of ethics and constructing a philosophy of success.

The art of the deal

On the surface, the book promises some insight about dealmaking. It is littered with boastful anecdotes of deals, with few actually usable lessons. However, it does show how our hero, Trump approaches everything through the lenses of deals.

The book is framed by two chapters. The opening chapter is a diary of a week, accounting for days filled with dealmaking. It portrays a man, who wakes up early, gets into his office, and spends the entire day calling people on the phone, furthering ongoing deals. Visibility to his family life is restricted to a few entries where he discusses his first wife, Ivana managing his projects. The final chapter brings some conclusion to the mentioned deals, even though many of them are not yet closed.

The second chapter, "Elements of the deal" is a collection of his wisdom. Some reasonably good advice, although some of it is strangely in contradiction with what he actually does in later chapters. The following chapters are chronological accounts of his childhood, the formative years of working for his father's residential real estate development companies, his first own real estate deals, and then the broadening of his enterprise beyond the familiar world of real estate.

Donald was the second son of Fred Trump, a homebuilder magnate. Fred had a very sharp focus on the business since his teenage years, had a knack for getting government subsidies, he scrutinized thoroughly the work of his subcontractors and controlled costs tightly. He is described as a real Scrooge, but in the kindest words possible. He groomed his first son, Freddy, to take over the business. However, Freddy was interested in everything but that, to the great disappointment of his father. Donald, on the other got along with his father really well:

Fortunately for me, I was drawn to business very early, and I was never intimidated by my father, the way most people were. I stood up to him, and he respected that. We had a relationship that was almost businesslike. I sometimes wonder if we’d have gotten along so well if I hadn’t been as business-oriented as I am.

However, there were issues with little Donald:

Even in elementary school, I was a very assertive, aggressive kid. In the second grade I actually gave a teacher a black eye—I punched my music teacher because I didn’t think he knew anything about music and I almost got expelled. I'm not proud of that, but it’s clear evidence that even early on I had a tendency to stand up and make my opinions known in a very forceful way. The difference now is that I like to use my brain instead of my fists.

Let’s be honest, he was a bully. Now he realizes that it was wrong to hit his teacher as an expression of disagreement on music. I just wonder if he ever realized that a 2nd grader's opinion might not be better than his teachers'.

Eventually his father decided to send him to military school to learn some discipline. After finishing school, he went back to work with his father.

After a few years of managing his father's housing projects, he decides he wants something more ambitious, and moves to Manhattan. He figures he needs to rub some shoulders with the elites of NYC, so he joins the most prestigious, exclusive club called ... Le Club.

Slowly he gets his foothold in Manhattan, builds the Grand Hotel for Hyatt, and then the Trump Tower.

Lessons in dealmaking

As the diary chapter shows, by the time the book is being written, he spends his days mostly outside of the realm of real estate, demonstrating that he graduated to being an universal moneymaker, exerting his midas touch to everything within reach. Let's hope we can figure out his secrets!

Some of the deals are simple, like buying stocks of Holiday Inn and then selling them at profit. Not much to learn, except that he made money, good for him!

Other entries in the diary shows that he is very focused on deals, like this one where he meets a random couple in the Trump Tower with David Letterman:

Letterman walks in, along with a cameraman, a couple of assistants, and a very nice-looking married couple from Louisville. We kid around a little, and I say what a great town I think Louisville is—maybe we should all go in together on a deal there.

Some entries are not even deals, I don't know what these are supposed to be, name dropping?

1:30 p.m. I tell Norma to call John Danforth, the Republican senator from Missouri. [...] Danforth isn’t in, but his secretary says he'll call back.

2:15 p.m. John Danforth calls back. We have a nice talk, and I tell him to keep up the good work.

6:00 p.m I excuse myself, because I am due at an early dinner, and it’s not the kind to be late for. Ivana and I have been invited, by John Cardinal O’Connor, to have dinner at St. Patrick’s Cathedral.

As we leave, I tell Ivana how impressed I am with the cardinal. He’s not only a man of great warmth, he’s also a businessman with great political instincts

Then there is this curious phone call:

3:45 p.m. The executive vice president for marketing at the Cadillac Division of General Motors is on the phone. He’s calling at the suggestion of his boss, John Gretenberger, the president of the Cadillac Motors Division whom I know from Palm Beach. Cadillac, it turns out, is interested in cooperating in the production of a new superstretch limousine that would be named the Trump Golden Series. I like the idea.

So, Grettenberger figures they want to make opulent limousines, with internals covered in gold, leather and wood, and, for added distinction, they want to name it after Trump and have it brandish the iconic name on every visible surface. Trump likes the idea!

The cars weren't in production by the time the book was published, so we are left wondering how big a success this cooperation got. It turns out, only 1-1 prototypes were made of the Trump Golden Series and the less opulent Trump Executive Series. Oh?

According to Grettenberger's biography Ready, Set, Go!, Trump pitched the idea that if Cadillac made limousines with his stylistic input, he would buy 50 of them to shuttle the high rollers in his hotels in NYC to his Atlantic City casinos. No wonder he liked the idea, it was his! They made 1-1 prototypes of both series, and waited for the purchase order to come in. Trump bought one of the prototypes, and gave various excuses for delaying the purchase order for the remaining 49. They eventually gave up on the project. Trump got a personalized limousine and Cadillac got a priceless lesson on The Art of the Deal.

Oh, about the casinos:

4:30 p.m. My last call is to Paul Hallingby, a partner at Bear Stearns who handled the $550 million in bond issues we did successfully for our two casinos in Atlantic City during 1985.

I'm no 80s tycoon, but $550 million sounds like a lot of debt for two casinos! I mean, that was a decade that sported interest rates in the teens. And in the chapter called "Elements of the deal", I learned about the importance of being conservative:

It’s been said that I believe in the power of positive thinking. In fact, I believe in the power of negative thinking. I happen to be very conservative in business. I always go into the deal anticipating the worst. If you plan for the worst—if you can live with the worst—the good will always take care of itself. [...] The point is that you can’t be too greedy. If you go for a home run on every pitch, you’re also going to strike out a lot. I try never to leave myself too exposed [...]

Ok, then that's got to be a reasonable amount of debt, he would never take the risk of overlevering the business!

The prime rate had been around 14 percent when I first started looking at property in Atlantic City. By mid-1986, it had dropped to 9 percent.

Ok, so Trump can get financing for 9%! Cool! One of his casinos made $35m operating profit the year he bought it, and he used $250m debt, which means an interest payment of about $23m, or 2/3 of operating profits. That leaves $12m for replacing broken chairs and dead light bulbs and any other maintenance expenses, as these are not included in operating profit. With this capital structure, it seems like there is even room for some net profit!

My problem with bank financing, even at these lower rates, was that I'd still be required to put myself personally on the line for the money. I didn’t find that appealing.

Ok?

As a result, I decided to seek public financing for the project, through a bond issue. The downside was that I'd have to pay a higher interest rate to attract buyers, but the upside was that once the issue sold out, I wouldn’t be personally liable.

Oh?

Interest payments on the financing came to just above $30 million a year. That was about $7 million a year more than I'd have paid for bank financing, but to me it was money well spent.

$30 million! That's over 85% of operating profits! Man! If the coming years are anything but spectacular for the casino, it will go under water! Let's hope for the best!

For the full year, our gross operating profit was nearly $58 million, or $20 million more than Harrah’s had projected.

Phew! Looks like it's gonna work out, unless someone opens a lavish hotel-casino nearby that would grab all the gamblers' attention and $$$.

[...] the Taj Mahal on the Boardwalk, designed as the largest and most lavish hotel-casino in the world, [...]

Oh-no!

[...] I hope to have the Taj open by October 1988

Oh-kay? So Trump is building the largest and most lavish casino next door to his other casinos? I wonder, how did that work out? All 3 casinos went bankrupt by 1992.

Let our lesson in the art of the deal be: If lever your casino with so much non-recourse (meaning you won't be liable if the business goes down) debt that only an exceptionally good run can make it stay in business, we will end up with either

  1. an exceptionally good casino, or
  2. no financial liability for the bankrupt business.

Heads, we win, tails, they lose.

Maybe there's one more lesson here: Avoid being your own competition? I don't know, I'm just spitballing here, let's look at what the experts say about the risk of competition during another deal: opening the Grand Hotel in a joint venture with Hyatt.

I pointed out that this was a rather big and risky investment the bank was making, and that one way to further protect the loan might be to insist on a restrictive covenant, so that Hyatt couldn’t throw up a second hotel two years later, right down the street. The banker saw the implications immediately. He stormed into the room where the Hyatt

people were sitting, and he said, ”Hey, fellas, we’re putting up tens of millions of dollars, which is a lot of money, and we're not going to make this loan unless we get a covenant from Hyatt saying you won’t open up any other hotels in New York.”

Trump loves casinos. (This was before they all went bankrupt.) As regulations of Atlantic City does not allow him to operate more than 3 casinos, he decides to try something else:

The government of New South Wales is in the midst of choosing a company to build and operate what they envision as the world’s largest casino. We're a frontrunner for the job

4:30 p.m. Nick Ribis calls from Australia. He tells me things are going very well on our negotiations to be designated builder and operator of the world’s largest casino.

Sounds great, how did it go?

The idea of running a business which is a twenty-four-hour plane trip from New York City just didn’t make sense—particularly when I have so much to occupy my attention in my own backyard. Shortly before the decision was to be announced by officials in New South Wales, I let them know that I was withdrawing my bid.

Our lesson: No matter how well you plan out a deal, something unforeseeable can crop up at the last moment. Something like Australia being far away, you just can’t prepare for that. Should that happen, you must be able to walk away from the deal.

Our next lesson on dealmaking: anything can be a deal!

I saw a national news report by Tom Brokaw about this adorable little lady from Georgia, Mrs. Hill, who was trying to save her farm from being foreclosed. Her sixty-seven-year- old husband had committed suicide a few weeks earlier, hoping his life insurance would save the farm, which had been in the family for generations. But the insurance proceeds weren’t nearly enough.

Sad! He decides to call up the bank:

I called and got some vice president on the line. I explained that I was a businessman from New York, and that I was interested in helping Mrs. Hill. He told me he was sorry, but that it was too late. They were going to auction off the farm, he said, and ‘‘nothing or no one is going to stop it. That really got me going. I said to the guy: “You listen to me. If you do foreclose, I'll personally bring a lawsuit for murder against you and your bank, on the grounds that you harassed Mrs. Hill’s husband to his death.”

All of a sudden the bank officer sounded very nervous and said he’d get right back to me. Sometimes it pays to be a little wild. An hour later I got a call back from the banker, and he said, “Don’t worry, we're going to work it out, Mr. Trump.”

So, the bank said, "no thanks, we don't want the money, we'd like to go to the auction" because

  1. they love the thrill of it,
  2. they are evil and just want to see the lady suffer,
  3. what is even money, just a piece of paper!

Oh these bankers! But Trump with his bad boy attitude makes them run and saves the day. He threw a fundraiser, raised more than $100,000, threw a party in the Trump Tower to celebrate, and all the media reported about it. Sources do not agree on how much he contributed, but it's around $40,000.

Our lesson: if you are doing something good, make sure it is something that is already covered by Tom Brokaw, and then keep it very visible so the press has something to report about. It's good PR.

Self-Promotion

With this, we reached one very important lesson: it is not enough to be great, everyone else must know about it too!

Tens and hundreds of millions are thrown around throughout the book, page after page, so when a deal is only about a few hundred thousand dollars, it really makes me wonder: why bother doing such a small project? Why bother writing an entire chapter on it?

The Wollman Rink is a popular skating rink in Central Park, NYC. City officials decided to rebuild it in the 1980. 6 years and many million dollars later, there was still no end in sight. It was a proper disaster. Trump offered to finish it within 6 months, paying for the building and then leasing it from the city to operate it profitably. Mayor Ed Koch responded in a public letter with a counteroffer. He did not want Trump to operate the rink as he wanted it to be priced very

accessibly, even at the risk of being unprofitable. He did offer Trump the opportunity to donate $3 million towards the rebuilding and to supervise the work.

He totally underestimated the press reaction. First, the press thrives on confrontation. They also love stories about extremes, whether they’re great successes or terrible failures. This story had it all. [...] Even I was surprised at how totally the press took my side. Obviously, that doesn’t always happen. But this time, within three days, there were

dozens of articles and editorials attacking Koch for his reaction to my offer.

Sure enough, the tide turned, overnight. No sooner did the press jump on Koch’s case than he reversed field completely. Suddenly, the city was virtually begging me to take on the Wollman Rink job.

I suggested a simple solution. I'd put up all of the money for the construction of the rink myself. In turn, I'd be reimbursed, over as many years as it took, from any profits the rink earned. In other words, I'd not only supervise construction, I'd also lend the city $3 million for an indeterminate period—and forever if the rink didn’t prove profitable.

If the rink does make money, I'll use it to reduce my loan. I'm not looking for personal profit. In fact, if I ever do get my money back, I'll give any subsequent profits to charity.

Dozens of newspapers as far away as Miami, Detroit, and Los Angeles ran

long pieces about the Wollman Rink saga. Time magazine devoted a full

page in its ‘‘Nation’’ section to the story. It was a simple, accessible

drama about the contrast between governmental incompetence and the power

of effective private enterprise.

Trump called in a press conference for the concrete-pouring. Invited Henry Stern, the NYC parks commissioner, too. Only one thing was amiss, the actual concrete-pouring:

If we can’t have a real concrete-pouring, at least we’ll have a ceremonial one. A couple of workmen pull over a wheelbarrow full of wet concrete and point it down toward us. Henry and I shovel some concrete onto the pipes while the photographers click away. As many times as I've done these things, I have to say I still find them a little ridiculous. Think of it: a couple of guys in pinstripe suits shoveling wet concrete. But I like to be accommodating. As long as they want to shoot, I'll shovel.

4 months later, by the time the temperature dropped below 55F, the rink as ready, and the costs stayed well below the projected $3 million. It was a huge success. Trump operated it at a profit, which he donated to charity. Why? He does not exactly tell us the reason.

But we can do the math: the rinks makes a few hundred thousand dollars of profit, that's not something that's gonna make a difference for someone who was supposedly a billionaire by that time. However, it exposes the Trump brand to half a million visitors every year. People, who are paying to be there, having a great time, and seeing the Trump logo everywhere. That's good advertising, for the price of about $1 per visitor. But that's just half the story.

It was hugely publicized project, he held press conferences all the time, for every possible occurrence, and if there was no occurrence for it, he made one up (eg. fake concrete-pouring).

There were those who said I went a little overboard holding press conferences about Wollman Rink. Perhaps they’re right, but I can only say that the press couldn’t get enough of this story. At least a dozen reporters showed up for every press conference we held.

There were stories in every newspaper with headlines like TRUMP HAS AN ICE SURPRISE FOR SKATERS and TRUMP PUTS THE ICING ON WOLLMAN CAKE.

It had a powerful message: We build competently, on time, within budget. You can rely on us for your real estate development needs.

So powerful a message that he even got his subcontractors to forgo their profits, making the savings even more impressive and the story even more impactful. In exchange for their profits, they get credited for being the expert builders of the rink. That's how valuable good

publicity can be.

Except, Trump may have forgotten to mention his subcontractors during the press conferences, taking all the credit for himself:

HRH was promised publicity in exchange for doing the work on Wollman Rink, but it never got so much as a mention from Trump for its work.

“He can’t have two people standing on the podium. He can’t have somebody even getting the silver and the bronze, He's gotta get the gold, the silver and the bronze all at one time,” said Nusbaum.

This is a big lesson from Trump: As long as they are shooting, you shovel. It does not matter that there is no point shoveling, if you give them what they want, they give you what you want: publicity.

Most reporters, I find, have very little interest in exploring the substance of a detailed proposal for a development. They look instead for the sensational angle.

So you need to feed them the sensational: the most expensive, the biggest, the best. If you associate yourself with the most extravagant, even bad press can be good: while building the Trump Tower, he demolished some art deco reliefs that he previously promised to save and

donate to The Met, and then went back on the promise because destroying them was cheaper. The press ran with the story:

The stories that appeared about it invariably started with sentences like: “In order to make way for one of the world’s most luxurious buildings...” Even though the publicity was almost entirely negative, there was a great deal of it, and that drew a tremendous amount of attention to Trump Tower. Almost immediately we saw an upsurge in the sales of apartments. I’m not saying that’s a good thing, and in truth it probably says something perverse about the culture we live in. But I'm a businessman, and I learned a lesson from that experience: good publicity is preferable to bad, but from a bottom-line perspective, bad publicity is sometimes better than no publicity at all. Controversy, in short, sells.

What if you don't have the most extravagant thing, but still want to make things sensational? You can try lying!

I play to people’s fantasies. People may not always think big themselves, but they can still get very excited by those who do. That’s why a little hyperbole never hurts. People want to believe that something is the biggest and the greatest and the most spectacular. I call it truthful hyperbole. It’s an innocent form of exaggeration—and a very effective form of promotion.

But wait, isn't it bad if you lie? Nah, it's only bad if you get caught!

You can’t con people, at least not for long. You can create excitement, you can do wonderful promotion and get all kinds of press, and you can throw in a little hyperbole. But if you don’t deliver the goods, people will eventually catch on.

This is the Elon Musk principle: promise people the impossible, then deliver them something great and they won't be mad.

The way to make a lie more effective is to actually believe it. NYC's City Planning Commission hired Victor Palmieri to sell off the assets of Penn Central Railroad. The bidding went like this:

Trump: I'll take it for $62m.

Palmieri: We have 62! Anyone for 65? Can we get 65?

Starrett: $135m!

Trump: Don't listen to them!

Palmieri: Huh?

Trump: They don't have $135m.

Starrett: Yes we do!

Trump: Even if they do, they would not be able to successfully develop the site.

Palmieri: What makes you say that?

Trump: I happen to genuinely believe that.

Palmieri: Oh, ok.

Starrett: Wait, what's happening?

Trump: You want a very serious and very committed developer. That's me.

Palmieri: That's right, sold for $62m to the gentleman with the hair!

Starrett: SMH

You are not a liar if you happen to genuinely believe the thing you just made up.

Philosophy

Our hero claims to be a great success (which claim, as we just learned, may or may not be a 'truthful hyperbole'), how does he explain his success?

Life is very fragile, and success doesn’t change that. If anything, success makes it more fragile. Anything can change, without warning, and that’s why I try not to take any of what’s happened too seriously. Money was never a big motivation for me, except as a way to keep score. The real excitement is playing the game. I don’t spend a lot of time worrying about what I should have done differently, or what's going to happen next.

Very Marcus Aurelius. What does Trump do when things does not go his way? Like when he wanted to buy a building (the one with the art deco reliefs) to make way for the Trump Tower, but Franklin Jarman, the CEO of the company owning the building refused to sell it? He wrote a letter, saying thanks for the meeting. Such gratitude. What else did he do? Sent another letter a few months later, and another one, and another one, offering different deals. Much persistence, so relentlessness. Has Jarman changed his mind? No! But the company's board did change their mind about Jarman, and replaced him with John Hanigan, whose job was to save the company from going bankrupt by selling its assets. Trump called him, and he was like "You're the one writing all those letters! When do you want to meet?". A nice parable of being relentless when facing a lack of encouragement.

Trump tried to enroll a star athlete, Lawrence Taylor for his football team, offering a huge bump in pay to leave the NFL after Taylor's current contract expires. Taylor signed up with Trump, but then the NFL overbid Trump. How did Trump react? He was happy about forcing the NFL to increase Taylor's salary significantly. He was also happy about the $750,000 NFL paid him for letting Taylor out of his contract, but let's just forget about this for a moment while I make a point about him being positive even when things don't go his way.

Does this mean Trump is the new philosopher emperor? Maybe not, maybe it means that the margin between a stoic and a narcissist is not as wide and defined as anyone would like to believe. You can weave a positive narrative around every adversity. You can hypnotize yourself to look for the opportunity in each and every circumstance. Looks like both stoicism and

narcissism uses very similar tools, the only difference being the end goal: virtue for the stoic, status for the narcissist.

Ethics

So, if you are not a stoic, that means you are not constrained by the rules of virtue. You can use 'truthful hyperbole' if it helps your cause. Or you can lie and call your lies 'truthful hyperbole'.

Remember the fake concrete-pouring? That was a cute gimmick to impress the press. Let’s up the ante! To build his first casino, Trump wanted to partner with someone who already knew how to run one. He was in negotiations with Holiday Inn, who was already operating one in Atlantic City. Everything was agreed upon, only the board approval was missing for the deal. They happened to have their annual meeting in Atlantic City, so they thought they should make a visit to the construction site before making the decision. The thing is, they may have been under the impression that the construction was further ahead than it was in its physical reality. Trump does not exactly say how this happened, I guess some “truthful hyperbole” was involved. Anyways, he did not want to disappoint:

I called in my construction supervisor and told him that I wanted him to round up every bulldozer and dump truck he could possibly find, and put them to work on my site immediately. Over the next week, I said, I wanted him to transform my two acres of nearly vacant property into the most active construction site in the history of the world. What the bulldozers and dump trucks did wasn’t important, I said, so long as they did a lot of it. If they got some actual work accomplished, all the better, but if necessary, he should have the bulldozers dig up dirt from one side of the site and dump it on the other. They should keep doing that, I said, until I gave him other instructions.

So the board came to inspect the site:

I’ll never forget one of them turning to me, shaking his head, and saying, ‘‘You know,it’s great when you're a private guy, and you can just pull out all the stops.”A few minutes later, another board member walked over to me. His question was very simple. ‘‘How come,” he said, *‘that guy over there is filling up that hole, which he just dug?" This was difficult for me to answer, but fortunately, this board member was more curious than he was skeptical. The board walked away from the site absolutely convinced that it was the perfect choice.

The board was so impressed with his fake construction capabilities that they signed the partnership a couple weeks later.

A good skill to have is the ability to manipulate people around you. It makes your life easier. In military school, Trump had a drill sergeant:

He didn’t take any back talk from anyone, least of all from kids who came from privileged backgrounds. If you stepped out of line, Dobias smacked you and he smacked you hard. Very quickly I realized that I wasn’t going to make it with this guy by trying to take him on physically. A few less fortunate kids chose that route, and they ended up getting stomped. Most of my classmates took the opposite approach and became nebbishes. They never challenged Dobias about anything. [...] I figured out what it would take to get Dobiason my side. In a way, I finessed him. It helped that I was a good athlete, since he was the baseball coach and I was the captain of the team. But I also learned how to play him. What I did, basically, was to convey that I respected his authority, but that he didn’t intimidate me.

So Trump learned how to be on good terms with people of unchallengeable power, authority and explosivity. Sounds useful if you are dealing with dictators. It opens up opportunities not available to people who want their peers to be in good standing.

There are a few examples in the book where he associates with people of dubious reputation. Irving, a real estate manager is described by Trump thusly:

He was one of the greatest bullshit artists I've ever met, but in addition to being a very sharp talker and a very slick salesman, he was also an amazing manager.

He was warned that Irving was a con man, who has had lots of trouble with the law. He figured that no one under Irving's management would be able to steal, so he only needs to keep an eye on Irving. He was sure Irving was stealing from him, but he never caught him, and just regarded it as a cost of business. He paid him $50,000, and assumed he stole another $50,000. If he ever caught Irving stealing, he would've fired him immediately, but that never happened. What did happen was that the funeral fund to which every employee contributed vanished. Everyone was sure Irving took it. Trump was sure Irving took it. But stealing from other employees turned out not to be a fireable offense:

 Irving was a classic. He had problems, but he was a classic.

Then there was Roy Cohn, a lawyer whom he met in Le Club:

He was no Boy Scout. He once told me that he’d spent more than two thirds of his adult life under indictment on one charge or another.

He was a truly loyal guy—it was a matter of honor with him—and because he was also very smart, he was a great guy to have on your side.

Just compare that with all the hundreds of “respectable” guys who make careers out of boasting about their uncompromising integrity but have absolutely no loyalty. They think only about what’s best for them and don’t think twice about stabbing a friend in the back if the friend becomes a problem.

Elsewhere, Trump derides Ed Koch for his lack of integrity: the NYC mayor called his friend Donald Manes a crook once it turned out Manes was engaging in kickback schemes during his Queens borough presidency.

For Trump, being loyal beats being ethical every single time.

Status

So, Trump loves to surround himself with people who show great loyalty. Who would have his back no matter what. And he likes people who say things he wants to hear.

When he met Cohn, Trump immediately went on a tirade about lawyers (knowing well that Cohn himself is one) who always play safe and who want him to settle a lawsuit the government filed against his company, and he wants to fight. He explains how the company is being accused of

discriminating against black tenants. Cohn replied:

My view is tell them to go to hell and fight the thing in court and let them prove that you discriminated, which seems to me very difficult to do, in view of the fact that you have black tenants in the building. I don’t think you have any obligation to rent to tenants who would be undesirable, white or black, and the government doesn’t have a right to run your business.

Cohn was willing to tell Trump what he wanted to hear. He told him that they should countersue

for $100m.

We ended up making a minor settlement without admitting any guilt. Instead, we agreed to do some equal-opportunity advertising of vacancies for a period of time in the local newspaper. And that was the end of the suit.

Let's recap what happened here:

Lawyers: Our best course of action would be to settle.

Trump: I want to fight the government.

Lawyers: You can't win, you should settle.

Trump: You're fired!

Roy Cohn: You should totally fight the government.

Trump: You're brilliant!

[years later]

Roy Cohn: You can't win, you should settle.

Trump: Wait, this thing is still going on? Whatever, I don't care!

If you are doing what Trump wants, you are brilliant, if you don't do it, you are useless. Whether you are right or wrong does not actually matter.

So, he loves surrounding himself with people who praise him. When a sycophant is praising you, they are doing it because they are smart enough to realize how great you are. And if they are so smart, you should listen to them, whatever they say. Have you ever wondered where Trump gets his left-field lore and odd takes about various topics? This might just be one explanation for that.

When you are optimizing for status, you want to make other people think you are high status. You can do that by telling them how great you are, but they might not believe you. They might think you are just full of it and obnoxious, so this is not a foolproof method.

You can do one better by having other people telling everyone how great you are. Sometimes the media is willing to do that, but sometimes they do the opposite. Your loyal sycophants on the other hand, they will reliably talk you up. But if they themselves are not really high status people, others may just not care about their opinion on you, no matter how great they think you are.

So, what you do is, you get high status people to talk you up. One method is, telling everyone about how amazing, brilliant people your sycophants are. That way you raise their status, and they can raise your status in return. That's the perpetuum mobile of social status.

Conclusion

This is it, Machiavelli's review of The art of the Donald.

This one is not the book to learn about real estate development. Not even the best one to learn about the life of Donald J. Trump. What this book offers is a rare look inside Trump's thinking.

He plays the social metagame: lying is only bad when you are caught, lawsuits are tactical instruments to block your opponents, and bankruptcy law is a tool to make your creditors take the downside while you get the upside. While I do not think he is a brilliant mastermind, he has certainly figured out how to navigate and exploit social structures in a way and scale no one else does. Is this antisocial behavior, or is this post-ethical rationality?